IUPAC Name - (R)-(6-methoxyquinolin-4-yl)((2S,4S,8R)- 8-vinylquinuclidin-2-yl)methanol Formula - C20H24N2O2 Molar Mass - 324.417 g/mol Melting Point - 177 degrees Celsius ( 351 degrees Fahrenheit) Boiling Point - 66.4 degrees Celsius Half Life - 18 hours Solubility - Slightly(in water) Stability - Sensitive to light, otherwise it is stable Physical State - White / Off-White Amorphous Powder Alkaloid - Crystalline (from bark of Cinchona tree) Smell -Odorless Flammable - Slightly Density - N/A
Quinine Structure
Origins and Uses
Quinine was originally used by Quechua Indians to help prevent shivering. They came across Quinine by using the bark off of Cinchona trees. Europeans first began experimenting with Quinine in the early 17th century. It was first used to fight malaria in 1631 in Rome. Agostino Salumbrino was the first man to test the idea of using Quinine to fight malaria. The Cinchona bark was the most popular item shipped from Peru at the time. Quinine officially got it's name in 1820 by French researchers Pierre Joseph Pelleiter and Joseph Bienaime Caventou. Eventually Peru outlawed the export of Quinine. The Dutch fought back by smuggling seeds of the cinchona tree. The Dutch began producing 97% of the worlds Quinine. Quinine was important for the colonization of African countries, and also for the soldiers in World War II. It can now be used to cure abnormal heart rhythms, muscle cramps, and headaches.
Synthetic Quinine
In 1944 American Chemists R.B. Woodward and W.E. Doering created the first lab made Quinine. After this several different forms have been made, but none are as efficient. It wasn't until 2001 that a fully stereochemically controlled synthesis of quinine was achieved by Columbia University's Gilbert Stork and his co-workers. In 2004 (60 years after Woodward and Doering's accomplishment) two new highly stereocontrolled syntheses of the natural product were unveiled. One was achieved by Harvard's Eric N. Jacobsen and his co-workers. The other came from Yuichi Kobayashi's group at Tokyo Institute of Technology in Yokohama, Japan.
Other Medical Uses
Quinine can be used for killing parasites, fungus, bacteria , germs , and insects. It can reduce fever and spasms. It also does a lot more such as regulating heart beats, stimulating digestion, and calming nerves. A recent study showed that it helps to dry secretions. Quinine is important because it can treat a variety of different problems, and it is a herbal medicine.
Non-Medical Uses
Quinine is used in beverages such as tonic water and Schweppes. It is in some carbonated drinks like San Pelligrino Chinotto. It is sometimes put into street drugs such as heroin and cocaine. It is used to cure some types of fish from white spots (infections) on their scales.
Where is it found? How is it obtained?
Quinine is made from the bark of a Cinchona tree. These trees can be found at their homes (in the tropical Americas) at elevations between 3,000 and 11,000 feet. There are forty different documented species in the South American forests. To obtain Quinine the bark must be ripped off of the trees that are six to eight years old. The collected bark is then dried in the sun. It is exported, and from then on it is turned into powder. To get pure quinine, the cinchona bark must first be mixed with lime juice (acidic), and then extracted with paraffin oil. It is filtered a few times, and then mixed and shaken with sulfuric acid. It is then mixed with sodium carbonate to neutralize the solution. Quinine sulfate, as a crystal, is the product. Ammonia is added to get the pure quinine by itself. The same tree can be used for several cycles before it needs to be tore out of the ground and replaced with a fresh tree.
Cinchona Tree
Cinchona Tree Bark
Reaction Tendencies
Quinine is pretty much stable, but it does react with some things. When Quinine is put into high vacuum pressure it will sublime. When it is diluted in H2SO4 , it gives off a bluish luminescent glow. It takes a lot of energy to dissolve Quinine in water. (1 gram dissolves in 1900ml of water, or in 760ml of boiling water.) Last but not least, it breaks down easily in carbon based solutions and in alcohol.
Chemical Properties
Quinine is a complicated compound. Overall the structure on Quinine is heterocyclic, with seven rings. Two of the rings are benzenes including one nitrogen (which is a bond). It then is attached to a string of carbons which leads it it to yet another group of carbons. All of the bonds in this structure are covalent.
Explanation of Structure
Bond Type - all bonds are covalent % composition by mass -
Carbon
74.05 %
Hydrogen
7.46 %
Nitrogen
8.63 %
Oxygen
9.86 %
% composition by number -
Carbon
41.6 %
Hydrogen
50.0 %
Nitrogen
4.1 %
Oxygen
4.1 %
Picture showing Covalent Bonding
Health Hazards
Some health hazards that come from taking quinine:
May cause respiratory tract irritation if inhaled
May cause skin irritations such as allergic contact dermatitis
May cause blindness, mydriasis, disturbed color perception, photo phobia, or sticky liquid to come out of eye
May cause kidney damage, nervous system depression, tinnitus and many more if ingested
If inhalation, eye contact, skin contact, or digestion of unsupervised Quinine dosages occur please seek medical aid immediately
3-D moving model of Quinine
Click the picture to see the 3D moving model.
Experiment
To see an experiment that was recently done on Quinine, please click the picture:
Glowing Liquid: Click to see why!!
Fun Facts
The Cinchona Tree has gotten the nickname "Holy Bark" because of it's healing powers.
Malaria was responsible for the deaths of seven different popes. If Quinine had been around these may have been avoided.
Quinine is used in tonic water, gin, and vodka.
Jello shots get their famous glowing color from the tonic water.
Quinine is illegal in Australia because it kills blood platelets.
Hundreds of Japanese soldiers died in WWII from lack of Quinine medication thats helps cure Malaria.
The first organic dye was made by William Henry Perkin while he was attempting to synthesize Quinine.
Quinine may cause death.
In the U.S and Germany, Quinine is limited to 83-85 parts per million.
Having Quinine may cause an abortion.
The renal (kidney failure) percent is 20.
When the Cinchona Tree's seeds were first smuggled and sold they cost $20.00 which was the same price as the island of Manhattan.
Recent News
On Wednesday October 22nd, two Civil War era dolls got specially examined for some surprising secrets. The two dolls named Lucy Ann and Nina were found to have papier-mache heads that were hollow. These dolls may have once held Quinine or Morphine. These two dolls were used to smuggle drugs past the Union blockades.
Catherine Wright checks the two bodies of the Civil War dolls
Other Names:
LegatrinNovaquinineStremaQuin-AminoQuiphileBy:Sarah
Quinine is made of crushed up of Cinchona Tree bark. This is a picture of the tree bark's powder.
Table of Contents
Properties:
IUPAC Name - (R)-(6-methoxyquinolin-4-yl)((2S,4S,8R)- 8-vinylquinuclidin-2-yl)methanolFormula - C20H24N2O2
Molar Mass - 324.417 g/mol
Melting Point - 177 degrees Celsius ( 351 degrees Fahrenheit)
Boiling Point - 66.4 degrees Celsius
Half Life - 18 hours
Solubility - Slightly(in water)
Stability - Sensitive to light, otherwise it is stable
Physical State - White / Off-White Amorphous Powder
Alkaloid - Crystalline (from bark of Cinchona tree)
Smell -Odorless
Flammable - Slightly
Density - N/A
Origins and Uses
Quinine was originally used by Quechua Indians to help prevent shivering. They came across Quinine by using the bark off of Cinchona trees. Europeans first began experimenting with Quinine in the early 17th century. It was first used to fight malaria in 1631 in Rome. Agostino Salumbrino was the first man to test the idea of using Quinine to fight malaria. The Cinchona bark was the most popular item shipped from Peru at the time. Quinine officially got it's name in 1820 by French researchers Pierre Joseph Pelleiter and Joseph Bienaime Caventou. Eventually Peru outlawed the export of Quinine. The Dutch fought back by smuggling seeds of the cinchona tree. The Dutch began producing 97% of the worlds Quinine. Quinine was important for the colonization of African countries, and also for the soldiers in World War II. It can now be used to cure abnormal heart rhythms, muscle cramps, and headaches.Synthetic Quinine
In 1944 American Chemists R.B. Woodward and W.E. Doering created the first lab made Quinine. After this several different forms have been made, but none are as efficient. It wasn't until 2001 that a fully stereochemically controlled synthesis of quinine was achieved by Columbia University's Gilbert Stork and his co-workers. In 2004 (60 years after Woodward and Doering's accomplishment) two new highly stereocontrolled syntheses of the natural product were unveiled. One was achieved by Harvard's Eric N. Jacobsen and his co-workers. The other came from Yuichi Kobayashi's group at Tokyo Institute of Technology in Yokohama, Japan.Other Medical Uses
Quinine can be used for killing parasites, fungus, bacteria , germs , and insects. It can reduce fever and spasms. It also does a lot more such as regulating heart beats, stimulating digestion, and calming nerves. A recent study showed that it helps to dry secretions. Quinine is important because it can treat a variety of different problems, and it is a herbal medicine.Non-Medical Uses
Quinine is used in beverages such as tonic water and Schweppes. It is in some carbonated drinks like San Pelligrino Chinotto.It is sometimes put into street drugs such as heroin and cocaine.
It is used to cure some types of fish from white spots (infections) on their scales.
Where is it found? How is it obtained?
Quinine is made from the bark of a Cinchona tree. These trees can be found at their homes (in the tropical Americas) at elevations between 3,000 and 11,000 feet. There are forty different documented species in the South American forests. To obtain Quinine the bark must be ripped off of the trees that are six to eight years old. The collected bark is then dried in the sun. It is exported, and from then on it is turned into powder. To get pure quinine, the cinchona bark must first be mixed with lime juice (acidic), and then extracted with paraffin oil. It is filtered a few times, and then mixed and shaken with sulfuric acid. It is then mixed with sodium carbonate to neutralize the solution. Quinine sulfate, as a crystal, is the product. Ammonia is added to get the pure quinine by itself. The same tree can be used for several cycles before it needs to be tore out of the ground and replaced with a fresh tree.Reaction Tendencies
Quinine is pretty much stable, but it does react with some things. When Quinine is put into high vacuum pressure it will sublime. When it is diluted in H2SO4 , it gives off a bluish luminescent glow. It takes a lot of energy to dissolve Quinine in water. (1 gram dissolves in 1900ml of water, or in 760ml of boiling water.) Last but not least, it breaks down easily in carbon based solutions and in alcohol.Chemical Properties
Quinine is a complicated compound. Overall the structure on Quinine is heterocyclic, with seven rings. Two of the rings are benzenes including one nitrogen (which is a bond). It then is attached to a string of carbons which leads it it to yet another group of carbons. All of the bonds in this structure are covalent.Explanation of Structure
Bond Type - all bonds are covalent% composition by mass -
Health Hazards
Some health hazards that come from taking quinine:Click the picture to see the 3D moving model.
Experiment
To see an experiment that was recently done on Quinine, please click the picture:Fun Facts
Recent News
On Wednesday October 22nd, two Civil War era dolls got specially examined for some surprising secrets. The two dolls named Lucy Ann and Nina were found to have papier-mache heads that were hollow. These dolls may have once held Quinine or Morphine. These two dolls were used to smuggle drugs past the Union blockades.References
Websites
"Quinine(130-95-0)". ChemicalBook.com. 21 Oct 2010. http://www.chemicalbook.com/ProductMSDSDetailCB9720330_EN.htm
"Quinine". caryacademy.org. 21 Oct 2010. http://web1.caryacademy.org/chemistry/rushin/StudentProjects/CompoundWebSites/2002/Quinine/default.htm
"Quinine". Edinformatics.com. 21 Oct 2010. http://www.edinformatics.com/math_science/science_of_cooking/quinine.htm
"Cinchona" herbs2000.com. 21 Oct 2010. http://www.herbs2000.com/herbs/herbs_cinchona.htm
"Quinine" Wikipedia. 21 Oct 2010. http://en.wikipedia.org/wiki/Quinine#History
"Quinine" chemicalland21.com. 21 Oct 2010. http://www.chemicalland21.com/lifescience/phar/(-)-QUININE.htm
"Quinine" Chemical and Engineering News. pubs.acs.org. 26 Oct 2010. http://pubs.acs.org/cen/coverstory/83/8325/8325quinine.html
"Recent News" Civil War dolls get X-rayed for signs of smuggling. news.yahoo.com. 28 Oct 2010. http://news.yahoo.com/s/ap/20101027/ap_on_re_us/us_civil_war_dolls_2
Images"Quinine" 3dchem.com. 21 Oct 2010. http://www.3dchem.com/molecules.asp?ID=102# "Cinchona Tree". Using bark to fight the bite. mhhe.com. 23 Oct 2010. http://www.mhhe.com/biosci/pae/botany/botany_map/articles/article_08.html
"Quinine Structure Picture". wikipedia.com. 21 Oct 2010. http://en.wikipedia.org/wiki/File:Quinine-2D-skeletal.png
"Glowing Liquid". Glow in the Dark Drinks: Spring Break. chemistry.about.com. 23 Oct 2010. http://chemistry.about.com/b/2008/03/20/glow-in-the-dark-drinks-spring-break.htm
"Powder and Bottle". How to make Tonic Water. summitsips.com. 26 Oct 2010. http://summitsips.com/2009/10/how-to-make-tonic-water
"Covalent Bonding". Bonding. ider.herts.ac.uk. 26 Oct 2010.http://www.ider.herts.ac.uk/school/courseware/materials/bonding.html
Video"Fluorescence Spectroscopy of Quinine". MeasureNetTechnology. 23 Oct 2010. Youtube.com. http://www.youtube.com/watch?v=aqKXHJzjhBI